Grignard reagent

Chem.

any of the group of reagents produced by the interaction of magnesium and an organic halide, usually in the presence of an ether, and having the general formula RMgX, where R is an organic group and X is a halogen: used in the Grignard reaction.

[1900-05; see V. GRIGNARD]

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▪ chemistry

 any of numerous organic derivatives of magnesium (Mg) commonly represented by the general formula RMgX (in which R is a hydrocarbon radical: CH₃, C₂H₅, C₆H₅, etc.; and X is a halogen (halogen element) atom, usually chlorine, bromine, or iodine). They are called Grignard reagents after their discoverer, French chemist Victor Grignard (Grignard, Victor), who was a corecipient of the 1912 Nobel Prize for Chemistry for this work.

      Grignard reagents commonly are prepared by reaction of an organohalogen with magnesium in a nitrogen atmosphere because the reagent is very reactive toward oxygen and moisture. Organohalogens vary greatly in their rates of reaction with magnesium. For example, alkyl iodides generally react very rapidly, whereas most aryl chlorides react very slowly, if at all.

      Their chemical behaviour resembles that of carbanions (carbanion), species that contain a negatively charged carbon. Grignard reagents are strong bases (base) and strong nucleophiles (nucleophile). Thus, the Grignard reagent methylmagnesium bromide (CH₃MgBr) behaves as if it were equivalent to the methide ion (CH⁻₃).

      Except for hydrocarbons, ethers (ether), and tertiary amines (amine), almost all organic compounds react with Grignard reagents. Many of these reactions are used for synthetic purposes, notably those with carbonyl (carbonyl group) compounds (e.g., aldehydes (aldehyde), ketones (ketone), esters (ester), and acyl chlorides), with epoxides (epoxide), and with halogen compounds of certain metals (metal) (e.g., zinc, cadmium, lead, mercury) to form the alkyl derivatives of those metals.

Francis A. Carey

 

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